#30: Bow Wow & Diggy Simmons (TIE)

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One is a fresh-faced newbie looking to step outside the shadow of his hip-hop legend of a dad and stand on his own two in the game. The other went from teen novelty act to respected rapper (hey, Wayne saw enough to sign him to Young Money—so who are we to argue?!) and left a trail of swooning female hip-hop fans in his wake. They may be at completely different points in their career, but they’ve both shown us that you don’t need to be able to drive the whips you rap about in your songs in order to make your lyrics sound fresh.